Director of Technology, AI & Digital Transformation
Role details
Job location
Tech stack
Job description
- Develop and execute the company's AI roadmap and digital transformation strategy
- Identify practical applications for Artificial Intelligence across sales, marketing, service, operations, HR, finance, and customer experience
- Evaluate, implement, and optimize AI-powered tools, agents, copilots, and automation platforms
- Lead company-wide AI adoption initiatives and employee training programs
- Create governance, security, and compliance frameworks surrounding AI usage
- Stay ahead of emerging technologies and identify opportunities that create measurable business value
Automation Engineering & Process Optimization
- Design and implement workflow automation solutions that eliminate manual processes
- Develop scalable systems that improve efficiency, reporting accuracy, and employee productivity
- Integrate software platforms to streamline operations across departments
- Identify bottlenecks and engineer solutions that reduce friction and improve customer experience
- Build business intelligence, reporting, and analytics capabilities that support leadership decision-making
Technology Strategy & Innovation
- Develop and execute the company's long-term technology roadmap
- Align technology investments with strategic business objectives
- Partner directly with ownership and executive leadership on growth initiatives
- Evaluate emerging technologies and determine practical business applications
- Lead digital transformation projects from concept through implementation
Infrastructure, Cloud & Cybersecurity Leadership
- Oversee Microsoft 365, Azure, cloud infrastructure, networking, endpoints, and enterprise software systems
- Ensure high availability, reliability, scalability, and security across all locations
- Lead cybersecurity planning, risk mitigation, disaster recovery, and business continuity initiatives
- Maintain technology standards, policies, governance, and compliance practices
- Monitor evolving cybersecurity threats and implement proactive protection strategies
Systems Architecture & Integration
- Improve connectivity between business systems and dealership software platforms
- Design scalable technology ecosystems that support future growth
- Evaluate APIs, integrations, data flows, and enterprise architecture opportunities
- Create technology standards that improve efficiency and reduce redundancy
- Support data management, reporting, and business intelligence initiatives
Team Member Support & Technology Adoption
- Serve as the senior technology resource for the organization
- Lead technology onboarding, training, and adoption efforts
- Help employees leverage technology to improve performance and efficiency
- Foster a culture of innovation, curiosity, and continuous improvement
- Support multiple locations while maintaining exceptional service standards
Requirements
Do you have experience in Team leadership?, * Experience leading technology initiatives, digital transformation projects, or enterprise technology environments
- Strong understanding of Artificial Intelligence, Automation, Business Systems, Cloud Infrastructure, and Cybersecurity
- Experience implementing workflow automation, business process improvements, or systems integration projects
- Ability to translate business challenges into scalable technology solutions
- Strong project management and change management capabilities
- Exceptional communication and executive-level presentation skills
- Ability to balance strategic leadership with hands-on execution
Highly Desired Skills
AI Integration & Adoption, Generative AI Platforms, Microsoft Copilot Skills/Certification, Directory Service Integrations, AI Governance, Prompt Engineering, Workflow Automation, Power Automate, Power BI, Microsoft Azure, Microsoft 365 Administration/Certification, Business Systems Integration, API Integrations, Data Analytics, Business Intelligence, Cybersecurity, Cloud Computing, Enterprise Architecture, Digital Transformation, Process Improvement, Change Management, Systems Engineering, IT Leadership
Benefits & conditions
Pulled from the full job description
- Health insurance
- 401(k) matching
- Paid time off
- Employee discount
- Health savings account
- Life insurance
- Employee assistance program, We recognize that exceptional candidates may come from a variety of backgrounds, including:
- Director of Technology
- IT Director
- Head of Technology
- Director of Digital Transformation
- AI Integration Consultant
- Automation Engineer
- Solutions Architect
- Systems Engineer
- Enterprise Architect
- Business Systems Manager
- Technology Consultant
- Cloud Infrastructure Leader
- Operations Technology Leader
Why This Opportunity Is Different
This is a rare opportunity to build and influence the future technology strategy of a growing organization.
You'll have the ability to:
- Lead AI adoption across the business
- Build automation that impacts real-world operations
- Shape technology strategy at the executive level
- Work directly with ownership and senior leadership
- Influence business decisions through data and technology
- Help modernize and scale a multi-location organization
- Enjoy the products and lifestyle our customers are passionate about
Compensation & Benefits
- Competitive compensation based on experience
- Medical & Dental Insurance
- Health Savings Account (HSA)
- Traditional & Roth 401(k) with employer match
- Paid Time Off & Paid Holidays
- Life Insurance
- Employee Assistance Program (EAP)
- Additional voluntary insurance options
- Company-provided apparel
- Employee discounts on boats, powersports vehicles, parts, accessories, and apparel
- Access to demo units including pontoons, fishing boats, ATVs, side-by-sides, snowmobiles, personal watercraft, and Slingshots